%0 Journal Article %1 WOS:000458618500025 %A Faudone, Sonia N %A Paschoal, Alexandre R %A Jr, Paulo S Carvalho %A Ellena, Javier %A Martins, Felipe Terra %A Cuffini, Silvia L %A Ayala, Alejandro P %A Sperandeo, Norma R %C PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS %D 2019 %I ELSEVIER SCIENCE BV %J JOURNAL OF MOLECULAR STRUCTURE %K 11-dione; 19579-83-0; 5H-dibenz{[}b, FT-IR FT-Raman; Hot Powder TG-DTA}, X-ray and diffraction; f]lazepine-10 microscopy; stage {CAS %P 204-212 %R 10.1016/j.molstruc.2019.01.032 %T X-ray diffraction, vibrational and thermal study of dibenzazepinodione, a pharmacopeial impurity of oxcarbazepine %V 1182 %X The antiepileptic drug oxcarbazepine (OXC) was crystallized from various organic solvents, and mixtures of OXC crystals and red-orange particles were obtained. In view of the pharmaceutical relevance of OXC, this study focuses on the isolation and characterization of these red-orange crystals by structural single crystal (SCXRD), powder X-ray diffraction (PXRD) and Hirshfeld surface analysis, vibrational Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) and Density functional theory (DFT) calculations, and thermal methods of analysis simultaneous thermogravimetry-differential thermal analysis (TG-DTA) and hot stage microscopy (HSM). According to SCXRD, the red-orange crystals corresponded to a recently codified impurity of OXC, referred as dibenzazepinodione (DBZ) or impurity D in the United States and European Pharmacopoeias respectively, which crystallized in the orthorhombic Pccn space group with a half-molecule in the asymmetric unit. Hirshfeld surface analysis revealed that weak intermolecular contacts played an important role in the stabilization of DBZ packing. DBZ was also characterized through its mid-infrared and Raman spectra and its vibrational bands were assigned based on DFT calculations with the hybrid B3LYP functional, coupled with the 6-311++g (d,p) basis set. The TG-DTA and HSM results shed light on the behaviour upon heating of DBZ, revealing that this impurity is an unsolvated solid with high thermal-oxidative stability, which sublimed, melted locally and decomposed above 320 degrees C. The obtained results demonstrated that slow crystallization of OXC from solvents such as ethanol and dimethylsulfoxide, at 20-25 degrees C, in the presence or absence of ambient light afforded DBZ. The X-ray pattern based on the SCXRD data for DBZ is presented as reliable reference for its identification. (C) 2019 Published by Elsevier B.V.

@article{WOS:000458618500025, abstract = {The antiepileptic drug oxcarbazepine (OXC) was crystallized from various organic solvents, and mixtures of OXC crystals and red-orange particles were obtained. In view of the pharmaceutical relevance of OXC, this study focuses on the isolation and characterization of these red-orange crystals by structural [single crystal (SCXRD), powder X-ray diffraction (PXRD) and Hirshfeld surface analysis], vibrational [Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) and Density functional theory (DFT) calculations], and thermal methods of analysis [simultaneous thermogravimetry-differential thermal analysis (TG-DTA) and hot stage microscopy (HSM)]. According to SCXRD, the red-orange crystals corresponded to a recently codified impurity of OXC, referred as dibenzazepinodione (DBZ) or impurity D in the United States and European Pharmacopoeias respectively, which crystallized in the orthorhombic Pccn space group with a half-molecule in the asymmetric unit. Hirshfeld surface analysis revealed that weak intermolecular contacts played an important role in the stabilization of DBZ packing. DBZ was also characterized through its mid-infrared and Raman spectra and its vibrational bands were assigned based on DFT calculations with the hybrid B3LYP functional, coupled with the 6-311++g (d,p) basis set. The TG-DTA and HSM results shed light on the behaviour upon heating of DBZ, revealing that this impurity is an unsolvated solid with high thermal-oxidative stability, which sublimed, melted locally and decomposed above 320 degrees C. The obtained results demonstrated that slow crystallization of OXC from solvents such as ethanol and dimethylsulfoxide, at 20-25 degrees C, in the presence or absence of ambient light afforded DBZ. The X-ray pattern based on the SCXRD data for DBZ is presented as reliable reference for its identification. (C) 2019 Published by Elsevier B.V.}, added-at = {2022-05-23T20:00:14.000+0200}, address = {PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}, author = {Faudone, Sonia N and Paschoal, Alexandre R and Jr, Paulo S Carvalho and Ellena, Javier and Martins, Felipe Terra and Cuffini, Silvia L and Ayala, Alejandro P and Sperandeo, Norma R}, biburl = {https://www.bibsonomy.org/bibtex/2e87222056a170473e6403441cafd9de2/ppgfis_ufc_br}, doi = {10.1016/j.molstruc.2019.01.032}, interhash = {4e0207c60ec723627874121384d3c412}, intrahash = {e87222056a170473e6403441cafd9de2}, issn = {0022-2860}, journal = {JOURNAL OF MOLECULAR STRUCTURE}, keywords = {11-dione; 19579-83-0; 5H-dibenz{[}b, FT-IR FT-Raman; Hot Powder TG-DTA}, X-ray and diffraction; f]lazepine-10 microscopy; stage {CAS}, pages = {204-212}, publisher = {ELSEVIER SCIENCE BV}, pubstate = {published}, timestamp = {2022-05-23T20:00:14.000+0200}, title = {X-ray diffraction, vibrational and thermal study of dibenzazepinodione, a pharmacopeial impurity of oxcarbazepine}, tppubtype = {article}, volume = 1182, year = 2019 }